Carrie is an American reader of this blog, who has been selected to be one of the 300 people flying to Australia with OPRAH WINFREY in December.

Here she is looking fun and fabulous! I love that her bed is covered with a mess of clothes – that is exactly how my bed is when I’m playing dress-ups!

Carrie asked me to help style her, hoping to increase her chances of being selected to sit on the FRONT ROW of the Oprah audience. It sounded like such a cool and fun thing to be part of!

SO. Firstly, I didn’t simply want to bombard Carrie with latest styles and trends and simply say JUST WEAR THIS, THIS, AND THAT. I wanted to get to know her, and HOW and WHY she dresses the way she does.

Getting To Know Carrie
I asked Carrie to rummage through her wardrobe, put on a few of her favourite outfits, and get someone to take photos of her.

Instead she chose to rearrange her bedroom, prop up a huge mirror…and took the photos herself! In the same style as I do. I thought it was utterly hilarious!

She also wrote down a few notes about each outfit, which was great.

After I saw Carrie’s photos, I also really wanted to talk to her too.

I installed Skype on my computer, and then discovered that my old clunker of a computer didn’t have a built-in microphone. Which meant I had to go out to the shops to buy a headset.

Then, as I was working out the time zone difference between Carrie’s part of America, and my part of Australia, I discovered that Carrie lives on exactly the opposite side of the Earth to me. We are exactly 12 hours apart in time. So when it is 8am TODAY for me, it is 8pm YESTERDAY for Carrie (from my point of view). It took a few days to work out our best time to Skype, but it all worked in the end!

So I have learned this much about Carrie’s personality – she is heaps of fun and is happy to laugh about herself.

These are Carrie’s photos of how she dresses now.

Blue Dress – Carrie says she loves this dress because of the gathering at the shoulders. The length and fabric is a bit “muumuu-ish” and it so happens that she has TWO of these dresses because “all 30-somethings need 2 modern day muumuus you know?”

A “muumuu” is an American term for a dress that has little shape, especially, no waist.

Brown Dress – “I just LOVE this dress color and style. It’s not an everyday dress, but I wish it was.”

Black Dress – “This dress is very flattering. I wear it when I am in my event manager role at work. I have to look nice, but not outshine the host or guests.”

Black Dress – “Simple tank dress… with really cute ruffley-material-flowers on the front. It ties in the back.”

Magenta Top – She loves ruffles! Carrie wore this top to her last Oprah Winfrey show. “I LOVE this color. It’s kind of magenta meets plum, but I feel love when I see this color, this material. I just love it.”

Tee and Jeans – She lives in her jeans! “I could wear this outfit everyday! School drop offs, pick ups, running to grocery. It doesn’t draw attention, but it’s also not a jogging outfit. :) “

Her outfit photos were dotted with silly-fun photos like these and funny captions. I get a good feeling, that Carrie wants fashion to be a pleasure in her life…as it should be.

“I like to look great, not overdone for the occasion, but almost always would rather look overdressed than under. I’m thinking that my outfits are usually 70% complete. Accessories and cute jackets, etc. are where I start to fail slightly. I do need fashion help. Style wise, I’m game for anything, really!”

My Analysis

Carrie is a very lucky lady – she has a gorgeous body, with a desirable hourglass figure and great proportions. She has a waist, hips and boobs – exactly the kind of curves I wish I had more of. She’ll basically look great in anything!

I’ll be focusing on how to show off her waist to flatter her hourglass figure, without shouting out loud about it.

Carrie currently has a very simple and basic style, with a clear solution for each occasion. I really like that she appreciates that there are lots of occasions when you don’t want to stand out from the crowd.

I believe I was in that very same place about 5 years ago. I remember NOT being very confident about how to style an outfit. I wasn’t confident to buy expensive items, so I always bought lots of cheaper items.

Once I found something that looked good on me, I just stuck with it, bought similar items, and put outfits together using some simple and basic rules. My life was pretty busy with new babies, and practicality took precedence over “looking stylish”. But of course, my wardrobe got a bit tired after a few years, and I wanted to make a change.

So I went on a fashion journey and education – and now I’m loving the art of fashion and styling. And I’m really excited about taking Carrie along this journey too.

The Outfit Plan

I’m going to create a few outfits for Carrie. Here’s the run down of the critical themes she’ll need for the trip.

1) Outfit for the Oprah Show

2) Backup Outfit for the Oprah show (because everyone needs a backup outfit, in case you find out at short notice what you were planning was just not right for the context.)

3) Evening Wear – Going out to a nice dinner at a posh restaurant/cocktail party/reception. This could double as the back-up outfit.

4) Evening Wear – Casual, but smart.

5) Day wear – Casual, but smart.

6) Day Wear – Very casual summer wear!

I’m also going to include some travel-wear.

I have to factor in the WEATHER too. Carrie might find herself in Queensland (hot and humid), Sydney (hot and humid days, nights might be a bit cold) and Melbourne (well, anything goes for this city with 4 seasons in one day).

And I’ve got some rules. Every item has to be something that can be part of an ongoing wardrobe. (The only dress you should ever buy for only one-use only is your wedding dress!)

All the items have to be reasonably priced, relative to how often they can be worn.

Items cannot be part of a one-season style trend, because they will look like a DATE STAMP by next year.

The next step is for me to come up with some visuals to send to Carrie, for her to consider.